5,5'-Bis(benz-yloxy)-2,2'-[hydrazine-diylidenebis(methanylyl-idene)]diphenol.

The title azine mol-ecule, C28H24N2O4, lies about a center of inversion. The dihedral angle between the phenyl ring and the hy-droxy-substituted ring is 70.3 (5)°. The phenolic O-H group forms an intra-molecular hydrogen bond to the azine N atom.

Related literature

For the biological activity of azines, see: Gul et al. (2003 ▶); Kumaraswamy & Vaidya (2005 ▶). For related structures, see: Acrovito et al. (1969 ▶); Sithambaresan & Kurup (2011 ▶). For a related synthesis, see: Karmakar et al. (2007 ▶).

Experimental

Crystal data

C28H24N2O4

M = 452.49

Monoclinic,

a = 12.4748 (17) Å

b = 5.3630 (6) Å

c = 17.021 (2) Å

β = 90.699 (5)°

V = 1138.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.965, T max = 0.982

6320 measured reflections

2738 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.01

2738 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030171/ng5346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030171/ng5346Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H24N2O4	F(000) = 476
Mr = 452.49	Dx = 1.320 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1647 reflections
a = 12.4748 (17) Å	θ = 3.3–27.3°
b = 5.3630 (6) Å	µ = 0.09 mm−1
c = 17.021 (2) Å	T = 296 K
β = 90.699 (5)°	Needle, yellow
V = 1138.7 (2) Å3	0.40 × 0.20 × 0.20 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2738 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 28.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→14
Tmin = 0.965, Tmax = 0.982	k = −7→6
6320 measured reflections	l = −22→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.1778P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2738 reflections	Δρmax = 0.13 e Å−3
159 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (19)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.38498 (9)	0.6629 (2)	0.90134 (6)	0.0614 (4)
O2	0.36761 (13)	0.8385 (2)	0.62715 (7)	0.0803 (4)
N1	0.47835 (11)	0.5470 (3)	0.53460 (7)	0.0601 (4)
C1	0.23742 (16)	0.7056 (3)	1.04210 (9)	0.0663 (5)
H1	0.2071	0.5745	1.0138	0.080*
C2	0.22037 (16)	0.7219 (4)	1.12153 (10)	0.0699 (5)
H2	0.1786	0.6028	1.1464	0.084*
C3	0.26443 (16)	0.9118 (4)	1.16380 (10)	0.0665 (5)
H3	0.2522	0.9238	1.2175	0.080*
C4	0.32641 (17)	1.0844 (4)	1.12737 (11)	0.0742 (6)
H4	0.3573	1.2133	1.1563	0.089*
C5	0.34358 (16)	1.0684 (3)	1.04737 (11)	0.0706 (5)
H5	0.3862	1.1868	1.0228	0.085*
C6	0.29828 (14)	0.8791 (3)	1.00385 (9)	0.0553 (4)
C7	0.31240 (16)	0.8630 (3)	0.91687 (9)	0.0675 (5)
H7A	0.2439	0.8320	0.8911	0.081*
H7B	0.3410	1.0185	0.8970	0.081*
C8	0.40808 (13)	0.6150 (3)	0.82489 (9)	0.0505 (4)
C9	0.37165 (14)	0.7540 (3)	0.76205 (9)	0.0565 (4)
H9	0.3261	0.8887	0.7701	0.068*
C10	0.40315 (14)	0.6925 (3)	0.68662 (9)	0.0539 (4)
C11	0.46947 (13)	0.4874 (3)	0.67316 (8)	0.0512 (4)
C12	0.50273 (14)	0.3498 (3)	0.73856 (10)	0.0611 (5)
H12	0.5461	0.2110	0.7310	0.073*
C13	0.47411 (14)	0.4112 (3)	0.81321 (9)	0.0594 (5)
H13	0.4986	0.3173	0.8557	0.071*
C14	0.50412 (14)	0.4193 (3)	0.59605 (9)	0.0581 (4)
H14	0.5466	0.2782	0.5902	0.070*
H2'	0.3950 (16)	0.782 (4)	0.5836 (10)	0.096 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0707 (8)	0.0746 (8)	0.0390 (6)	0.0179 (6)	0.0081 (5)	0.0004 (5)
O2	0.1141 (12)	0.0833 (9)	0.0435 (7)	0.0295 (8)	0.0038 (7)	0.0089 (6)
N1	0.0613 (9)	0.0802 (10)	0.0388 (7)	−0.0018 (8)	0.0048 (6)	−0.0081 (7)
C1	0.0840 (14)	0.0642 (11)	0.0508 (10)	−0.0055 (10)	−0.0001 (9)	−0.0043 (8)
C2	0.0821 (14)	0.0747 (13)	0.0530 (10)	−0.0032 (10)	0.0090 (9)	0.0074 (9)
C3	0.0769 (13)	0.0786 (13)	0.0441 (9)	0.0174 (11)	0.0023 (9)	−0.0037 (9)
C4	0.0873 (15)	0.0703 (12)	0.0649 (12)	0.0022 (11)	−0.0031 (10)	−0.0198 (10)
C5	0.0802 (14)	0.0650 (12)	0.0670 (12)	−0.0016 (10)	0.0140 (10)	−0.0020 (9)
C6	0.0666 (11)	0.0569 (10)	0.0425 (9)	0.0132 (9)	0.0062 (8)	−0.0006 (7)
C7	0.0836 (14)	0.0724 (12)	0.0466 (10)	0.0215 (10)	0.0098 (9)	0.0025 (8)
C8	0.0510 (9)	0.0604 (10)	0.0403 (8)	−0.0010 (8)	0.0059 (7)	−0.0005 (7)
C9	0.0653 (11)	0.0584 (10)	0.0460 (9)	0.0109 (9)	0.0050 (8)	−0.0003 (8)
C10	0.0617 (11)	0.0589 (10)	0.0409 (8)	−0.0026 (8)	−0.0007 (7)	0.0034 (7)
C11	0.0521 (10)	0.0609 (10)	0.0406 (8)	−0.0033 (8)	0.0040 (7)	−0.0020 (7)
C12	0.0656 (12)	0.0687 (12)	0.0491 (10)	0.0157 (9)	0.0072 (8)	0.0002 (8)
C13	0.0661 (11)	0.0682 (11)	0.0439 (9)	0.0128 (9)	0.0053 (8)	0.0059 (8)
C14	0.0588 (11)	0.0715 (11)	0.0443 (9)	−0.0005 (9)	0.0037 (8)	−0.0057 (8)

O1—C8	1.3607 (17)	C5—H5	0.9300
O1—C7	1.431 (2)	C6—C7	1.496 (2)
O2—C10	1.3505 (19)	C7—H7A	0.9700
O2—H2'	0.874 (15)	C7—H7B	0.9700
N1—C14	1.288 (2)	C8—C9	1.376 (2)
N1—N1i	1.396 (2)	C8—C13	1.385 (2)
C1—C6	1.370 (2)	C9—C10	1.387 (2)
C1—C2	1.374 (2)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.397 (2)
C2—C3	1.359 (3)	C11—C12	1.394 (2)
C2—H2	0.9300	C11—C14	1.434 (2)
C3—C4	1.360 (3)	C12—C13	1.364 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.384 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.374 (3)
C8—O1—C7	117.41 (12)	O1—C7—H7B	110.1
C10—O2—H2'	107.8 (14)	C6—C7—H7B	110.1
C14—N1—N1i	113.47 (19)	H7A—C7—H7B	108.4
C6—C1—C2	121.17 (17)	O1—C8—C9	124.69 (15)
C6—C1—H1	119.4	O1—C8—C13	114.82 (14)
C2—C1—H1	119.4	C9—C8—C13	120.49 (14)
C3—C2—C1	120.14 (18)	C8—C9—C10	119.72 (16)
C3—C2—H2	119.9	C8—C9—H9	120.1
C1—C2—H2	119.9	C10—C9—H9	120.1
C2—C3—C4	119.79 (17)	O2—C10—C9	117.49 (15)
C2—C3—H3	120.1	O2—C10—C11	121.55 (14)
C4—C3—H3	120.1	C9—C10—C11	120.95 (15)
C3—C4—C5	120.15 (18)	C12—C11—C10	117.17 (14)
C3—C4—H4	119.9	C12—C11—C14	120.39 (16)
C5—C4—H4	119.9	C10—C11—C14	122.44 (15)
C6—C5—C4	120.57 (18)	C13—C12—C11	122.50 (16)
C6—C5—H5	119.7	C13—C12—H12	118.8
C4—C5—H5	119.7	C11—C12—H12	118.8
C1—C6—C5	118.16 (16)	C12—C13—C8	119.15 (16)
C1—C6—C7	120.25 (16)	C12—C13—H13	120.4
C5—C6—C7	121.58 (16)	C8—C13—H13	120.4
O1—C7—C6	107.98 (13)	N1—C14—C11	122.21 (17)
O1—C7—H7A	110.1	N1—C14—H14	118.9
C6—C7—H7A	110.1	C11—C14—H14	118.9
C6—C1—C2—C3	−0.3 (3)	C8—C9—C10—O2	−178.25 (16)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C10—C11	1.5 (3)
C2—C3—C4—C5	0.7 (3)	O2—C10—C11—C12	179.36 (16)
C3—C4—C5—C6	0.1 (3)	C9—C10—C11—C12	−0.4 (2)
C2—C1—C6—C5	1.1 (3)	O2—C10—C11—C14	0.2 (3)
C2—C1—C6—C7	−177.71 (17)	C9—C10—C11—C14	−179.61 (16)
C4—C5—C6—C1	−1.0 (3)	C10—C11—C12—C13	−0.9 (3)
C4—C5—C6—C7	177.77 (17)	C14—C11—C12—C13	178.29 (17)
C8—O1—C7—C6	179.40 (14)	C11—C12—C13—C8	1.1 (3)
C1—C6—C7—O1	−74.4 (2)	O1—C8—C13—C12	−179.31 (16)
C5—C6—C7—O1	106.85 (19)	C9—C8—C13—C12	0.1 (3)
C7—O1—C8—C9	4.0 (2)	N1i—N1—C14—C11	178.83 (17)
C7—O1—C8—C13	−176.67 (16)	C12—C11—C14—N1	−177.39 (17)
O1—C8—C9—C10	177.95 (16)	C10—C11—C14—N1	1.8 (3)
C13—C8—C9—C10	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2′···N1	0.87 (2)	1.84 (2)	2.625 (2)	148 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2′⋯N1	0.87 (2)	1.84 (2)	2.625 (2)	148 (2)